Category Archives: sissy training

Sissy boys, it’s about time you got real. And it’s about time you got into the phone sex you really need the most, sissy phone sex with me, a sexy Tranny. I already know the sissy secrets you hide from everyone else. Or you wouldn’t even be calling me. I know how much you fantasize about going all the way and transforming into a shemale. You can’t hide that you wish you could abandon your life as an inadequate man and give in to your dazzling dreams of becoming a real life TGirl. You have what it takes to start, sissies, but you need to begin phone sex transformation sessions where I will be your guide.

Look at my photos, you’re jealous, aren’t you? You want to be a sexy shemale and do nasty phone sex, seduce men, even become a tranny hooker. I’m familiar with the total trans lifestyle and can tell you the exact steps you need to take in order to leave behind your sissy self and become a tranny Goddess. You will need to walk and talk like a girl, look like a girl. Be a girl! By the time I’m done with you, no one will recognize you. You will be mine, a perfect shemale dolly.

I’m very supportive in my approach to transformation, but I expect results. The second you first slipped on a pair of panties has led you to this moment. It’s time to go even further than ever before. Sissy Phone Sex with a sexy shemale Goddess is the sexual destiny for you sissies. Don’t run away from it, my sissy boys! You know you want it and more importantly, need it.

Sissy Phone Sex with a dominant femdom who will make you into the sexy girl you always wanted to be, just what you’ve been looking for!
I love giving all the naughty cross dressers sissy assignments phonesex, how about we go shopping for a cute little outfit, from head to toe, silky panties, push up bra, thigh high stockings, and of course, shoes to begin your sissy phone sex transformation, you know this is making you want to touch your sissy clitty!
I always have lots of creative sissy phone sex assignments, and I’ve been handing out sissy bitch assignments to all the good little sissy submissives, and I’ve been playing lately with bombshells in corsets and latex, doesn’t that sound like your sissy fetish?
If you’ve ever had freaky fetish phonesex with me, you know how much I love giving you the unique beautiful female perspective on how to make you more feminine, pantyboy sissied and pantied for life training, and of course, strapons!
Just imagine how amazing it is on a sissy phone sex call with me, my sexy voice seducing you in your pretty ear, making you blush and simper when I put you in something to make you so sexy and womanly, indulging your inner sex kitten to make your femdom mistress happy, cross dressing for your Goddess!
Your total feminization journey begins with a call to the best sissy phone sex Goddess ever!
And just like any girl ever, sissies are so individual in what they like, so make sure to tell me just what kind of sissy you are, what gets you all horny, is it cock, strap ons, being pimped out, or just being made into a real girl?
Call me now for everything sissy, I absolutely adore and love indulging in feminization assignments and transgender as well as sissification phonesex!
Connie
AIM:CuckoldPhoneSex
YIM:CuckoldStoriesPhonesex

I put men in their place on a daily basis, so when they approach me with sissy training phone sex, I jump at the opportunity to teach them a thing or two. Many men have always possessed the trait to be a sissy but never knew what to do with their urge to dress and act as a woman. Some of them are married and have lived very masculine lives for years but always felt as if something was missing. I like to guide them with my mind and cock to make them into the best sissys they can be.

The first man who contacted me asking for sissy training phone sex was a guy named Tom. He was middle aged and expressed that he always has had the urge to be a sissy. When he was younger he would go into department stores and try on women’s panties. His urges just got worse as he got older and finally married and began wearing his wife’s panties and bra under his business suit during his work day. He told me he would go into the bathroom stall at work and rub his nipples through his intimate garments and imagine how it would feel to receive a facial.

He craved sissy phone sex training from a real tgirl so he came to the right place. My cock grew hard as I guided him to it and told him to open wide. I explained to him that every good sissy knows how to give an excellent blowjob on command. Once he got it nice and wet, I made him turn around so I could get a good look at his man pussy. It was gaping and ready for entry but I wasn’t going to give him my cock. Instead I got a ten inch dildo and shoved into him and watched him beg for mercy. Ready for you sissy training phone sex session with a dominant t-girl? Then call me Trinity at 1 888 8 FREAKY.

It’s Friday and I have a special night out planned for on our slutty sissy phone sex call. First thing I’m going to do is dress you up like the perfect slut. Stockings and garters with your little panties pulled over the garters. We need to be able to take them off without taking off those stockings. I think a proper slutty sissy needs to have big tits, so let’s get you a bra and stuff it full. A super short mini skirt and a sheer white blouse tied up to show your belly button.

Our first outing for the evening is to my favorite fetish shoe store. No sissy slut outfit would be complete without a pair of 5″ heeled cum fuck me pumps. After I pick out the perfect pair for you, it’s time to pay the man. Oh you forgot your wallet? I think there are other ways of paying up. He leads you to the back room, you get on your knees, and he pulls out his hard fat cock. With my hand on the back of your head, and my other hand on his cock, I tell you to open wide and start sucking like the slut you are. An experienced slut like you should have no problem taking his dick balls deep and sucking every drop of his precious cum. You better not miss any and ruin your outfit or his pants. Don’t make me spank you right here in front of everyone.

A quick stop at the salon for my girl to do your make up and hair. Shiny red cock sucking lipstick, extra long eyelashes, red rosy cheeks, and a long blonde wig complete your look. Perfect for our last stop at my favorite toy store. There is a special event tonight and you are the star. Not only are we going to try all the new dildos and strap-ons, all the guys are going to need someone to take care of their hard cocks. I tie you to a spanking bench, ass up in the air. I pull your head up by your collar so your mouth is available too. When you see them lining up for your sissy slutty boy pussy and your hungry mouth, you can’t wait for the real action to begin.

I get asked from time to time about what my favorite type of call to take is and honestly, I always find this to be so difficult to answer because each and every one of my callers is so very special in their own way! I will say this though; the most entertaining type of call I get are from my sissy sluts. Yep, that’s right, these guys want nothing more than to be turned into the perfect sissy bimbo and they know to call me because I’m the one that always gets the job done right! Let me guess, you’re one of the sissy boys, aren’t you? Sissy phone sex with me is perfect for you then!

How big of a sissy slut are you? I am looking for open minded sissy bimbos to have sissy phone sex with. Are you willing to push your boundaries and limits like never before? We can go as fast or slow as you’d like because when you want something done right you must be willing to explore it all. I’m talking about the whole package. I need my sissy to wear pretty lip gloss, nails painted, high heels and wigs… I love putting her in pretty bras and matching panties and of course dresses too.

Are you longing to be a perfect sissy? Well, when you call me for sissy phone sex I will turn you into just that. I am the perfect girl and I want to get you as close to perfect as possible, too. You do know, though, that it’s going to take a lot of work, don’t you? I mean, you’re not really a “mans” man, but you still have obstacles to overcome! Together, we’ll make you the sissy slut you’re supposed to be during our sissy phone sex session.

I’m ready today for some cock sucking sissy phone sex sluts. I know you’re out there. I talk to you all the time and I know what dirty whores you either are or want to be. And if you need to be turned into a whore, I’d be more than happy to give you a hand with that.

First, I have to ask you something – have you ever sucked cock? Have you ever had a big fat toy or dick in your pussy? If not, that’s gonna take some getting used to, so you’d better make sure you’ve practiced enough before you get to work on those real cocks. I believe in doing things big or not at all, so for your first time getting all dressed up and playing with real men, I think it would be fun to rent a hotel room for the weekend for you. Then we could place an ad online or something to get a bunch of guys to the room for you to play with! How many do you think you could service in a weekend, sissy slut? I mean, you’re probably going to have at least 10 per day. There will surely be tons of guys lining up for a free blow job or the opportunity to fuck a sissy whore like you.

I wonder which one of your holes will be used up first? Will your jaw be too tired to keep sucking cock? Will your pussy be too stretched out to let men keep fucking it? It’ll be tons of fun to find out. I can’t wait for you to feel like a real whore. Are you ready to become the sissy phone sex slut you were always meant to be?

Call 1 888 8 FREAKY and ask to talk to Lola to be transformed into your true sissy self!

Oh my goodness, I can’t wait to turn you into a dirty sissy phone sex slut. Have you been dying to have someone turn you into a cock sucking sissy faggot whore? Well, good news. You have found just the girl to make those dreams come true for you.

The first step in turning you into a sissy faggot is making you put on the panties and bra that I went out and bought for you. I got red because I am pretty sure everyone knows that red is the universal color of whores. And by the time I am done with you, that’s exactly what you are going to be!

Once you’re all dressed up, that’s when the real fun is going to begin, sissy whore! I’m going to bring over one of my friends with a HUGE dick and put you right down on your knees in front of him. And you’re going to open your mouth. Don’t resist and make this harder than it needs to be. I know that just as soon as you have that big fat cock in your mouth, you’re going to lose all of your inhibitions and start sucking like a good girl. If you’re really good, he might even let you swallow that juicy load for him.

Oh, and if you get too excited and shoot a tiny load in your panties (because let’s be real here – your dinky dick could never shoot a big load), you’re going to have to take your panties off and lick up every single drop of that. You need to learn right now that cum should never be wasted, even if it comes from a pathetic dick like yours.

Do you know who you are? Because I do! You are a girl trapped in a mans body. Call me for sissy phone sex so we can bring your inner slut to life. Thigh high’s,fish nets,garter belts,baby dolls,bra and panty sets are all the things you crave to wear for all those sexy guys who you are going to get on your knees for. Now that you are dressed for sissy phone sex its time to bring in the guys who have been waiting to have their long thick knobs polished by you whore. Im totally going to pimp you out, every owned sissy slut has to earn her keep! It turns you on to know that guys are going to pay me to use your wholes and you want to do a good job for me dont you? Of course you do! I cant wait to have sissy phone sex with you so I can put my hand on the back of your neck and force your head all the way down on that dick! Suck it good slut! Look at your clit standing straight up and leaking in your panties! The guys are willing to pay extra to use your pretty little man pussy. Go ahead and pull those panties to the side and spread those cheeks and take a real mans cock deep inside of you! This is what you have been craving for so long. You were born to be a sissy cock sucker whore you just need the right mistress to bring it out of you! Mistress Pepper will make all your sissy phone sex dreams cum true. Your clit cant stand it much longer its craving my ownership. I cant wait to make you squirt in those panties slut.

I love fucking with guys. It seems they’ll do anything to get a whiff of my bomb ass pussy. Anything. When I’m feeling really devious, I get into feminization phone sex. I’ll have them dress up so pretty just to amuse me. I like to go all the way with this fetish, so it’s not going to be just a bra and panties. Nope. I want you to go All. The. Way. So we need to pick out a hot outfit to make you look like a slutty party girl. You know what that looks like. A tight, seriously short denim miniskirt, a button down shirt tied at your waist showing off your sexy red bra. Some hot strappy heels. You’re either going to look fucking hot or fucking ridiculous. Either way, you’ll do it for me.

Once you’re all dressed up, then we get to hair and makeup. You’ll need a smoking hot wig, like maybe an asymmetrical bob or a long curly type. You’ll do your eyes in a dark smokey whore look, and of course very red lipstick. When you’re all done, it’s time to snap a selfie and send it to me so I can see you. I’ll save that for later *giggles* because you never know what you can use it for later. But for now we’ll stick to feminization phone sex. I want you to talk like a girl, act like a girl, and fuck like a girl. If I feel like phone fucking you, we’ll do that lesbian trick called scissoring. If not, I’ll get you to take a few big dicks while I watch and cheer you on. You really are a slut, you just needed the right outfit to make it come out.

So get your shit together and dial 1 888 8 FREAKY and let’s get this feminization phone sex party started!

One thing that a lot of sissy phone sex callers talk to me about is that they want to suck cock but have never done it. They are scared sometimes that they won’t do a good job once they finally have a dick in front of them. They know it’s a really important part of being a sissy so of course they want to learn to do it perfectly. I have a really great solution to that problem, though. I like sending my sissy callers down to the nearest glory hole to get some cock sucking practice in. I mean, there really is no better way to learn. It’s pretty anonymous, so if you don’t do a perfect job, it’s okay. They can’t see you and you can just try harder next time.

Another really good thing about going to a glory hole to practice sucking dick is that there is TONS of opportunity. You won’t suck just one dick every time you go. You will suck multiple dicks. You can basically stay there until you’ve had your fill for the night. Just think about it, sissy – cock after cock coming through that glory hole until your mouth is sore and your stomach is full of so many loads of cum.

You should know that I have faith in you. If you’re just starting your life as a sissy, of course you need practice. All of us aren’t born being awesome cock suckers. Sometimes, as with anything in life, you do need to practice. And that’s what I’m here for – to help you reach your full sissy potential in every way, not just cock sucking.

Grab your dildo to practice on and give me a call. Dial 1 888 402 8669 and ask to talk to Lola for sissy phone sex.

This service is brought to you by RPI, a joint venture with Palm Island, Inc. We accept VISA, MasterCard, Discover and American Express. All charges will appear on your credit card statement listed discretely as ‘Palm Island Inc dba RPI’.
For a complete description of our policies, view our Policies Page.

This site offers and promotes phone sex. Entering this site means you are of legal age to view (18 years and older), apply, and ask for services of an adult nature. If you are under the age of 18, please leave the site. All of the pictures on our site depict consenting individuals that are at least 18 years or older at the time of the photograph, and are fully consenting to the content in which they posed for, as per Title 18, Part I, Chapter 110, Section 2257 (18 U.S.C. § 2257).